Abstract
The new chiral auxiliary (R)-2-ethylthio-1-(phenylethyl)-(R)-binaphthyl phosphite, 1, and three stable Pd(0) olefin complexes containing this chelate, 2-4, have been synthesized. The structure of the maleic anhydride complex 3 has been determined by X-ray diffraction methods. Solution details for 2-4 and aspects of their dynamics have been elucidated via 2-D NMR spectroscopy. The fumaronitrile complex 2 exchanges intramolecularly, whereas the maleic anhydride and pentenedione derivatives, 3 and 4, respectively, exchange intermolecularly. Ligand 1 has been used as auxiliary in the Pd, Rh, and Ir regio- and enantioselective allylic alkylation reactions of PhCH=CHCH(OAc)R, R = H, Me, Et, with the anion of dimethyl malonate. Modest to good selectivities are reported.
| Original language | English |
|---|---|
| Pages (from-to) | 4591-4597 |
| Number of pages | 7 |
| Journal | Organometallics |
| Volume | 18 |
| Issue number | 22 |
| Publication status | Published - Oct 25 1999 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
Chiral Phosphite-Thioether Complexes of Palladium(0). Comments on the Pd, Rh, and Ir Regio-and-Enantioselective Allylic Alkylations of PhCH=CHCH(OAc)R, R = H, Me, Et. / Selvakumar, Kumaravel; Valentini, Massimiliano; Pregosin, Paul S.; Albinati, Alberto.
In: Organometallics, Vol. 18, No. 22, 25.10.1999, p. 4591-4597.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Chiral Phosphite-Thioether Complexes of Palladium(0). Comments on the Pd, Rh, and Ir Regio-and-Enantioselective Allylic Alkylations of PhCH=CHCH(OAc)R, R = H, Me, Et
AU - Selvakumar, Kumaravel
AU - Valentini, Massimiliano
AU - Pregosin, Paul S.
AU - Albinati, Alberto
PY - 1999/10/25
Y1 - 1999/10/25
N2 - The new chiral auxiliary (R)-2-ethylthio-1-(phenylethyl)-(R)-binaphthyl phosphite, 1, and three stable Pd(0) olefin complexes containing this chelate, 2-4, have been synthesized. The structure of the maleic anhydride complex 3 has been determined by X-ray diffraction methods. Solution details for 2-4 and aspects of their dynamics have been elucidated via 2-D NMR spectroscopy. The fumaronitrile complex 2 exchanges intramolecularly, whereas the maleic anhydride and pentenedione derivatives, 3 and 4, respectively, exchange intermolecularly. Ligand 1 has been used as auxiliary in the Pd, Rh, and Ir regio- and enantioselective allylic alkylation reactions of PhCH=CHCH(OAc)R, R = H, Me, Et, with the anion of dimethyl malonate. Modest to good selectivities are reported.
AB - The new chiral auxiliary (R)-2-ethylthio-1-(phenylethyl)-(R)-binaphthyl phosphite, 1, and three stable Pd(0) olefin complexes containing this chelate, 2-4, have been synthesized. The structure of the maleic anhydride complex 3 has been determined by X-ray diffraction methods. Solution details for 2-4 and aspects of their dynamics have been elucidated via 2-D NMR spectroscopy. The fumaronitrile complex 2 exchanges intramolecularly, whereas the maleic anhydride and pentenedione derivatives, 3 and 4, respectively, exchange intermolecularly. Ligand 1 has been used as auxiliary in the Pd, Rh, and Ir regio- and enantioselective allylic alkylation reactions of PhCH=CHCH(OAc)R, R = H, Me, Et, with the anion of dimethyl malonate. Modest to good selectivities are reported.
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M3 - Article
VL - 18
SP - 4591
EP - 4597
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 22
ER -